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36945-98-9,MFCD01689072
Catalog No.:AA00BZ7J

36945-98-9 | Icilin

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1mg
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10mg
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25mg
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50mg
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250mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BZ7J
Chemical Name:
Icilin
CAS Number:
36945-98-9
Molecular Formula:
C16H13N3O4
Molecular Weight:
311.2921
MDL Number:
MFCD01689072
SMILES:
O=C1NC(=CCN1c1ccccc1O)c1cccc(c1)[N+](=O)[O-]
Properties
Computed Properties
 
Complexity:
502  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
2.2  

Downstream Synthesis Route
Literature

Title: Activation of TRPV3 by Wood Smoke Particles and Roles in Pneumotoxicity.

Journal: Chemical research in toxicology 20180521

Title: TRPM8 activation attenuates inflammatory responses in mouse models of colitis.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20130430

Title: Lack of transient receptor potential melastatin 8 activation by phthalate esters that enhance contact hypersensitivity in mice.

Journal: Toxicology letters 20130313

Title: TRPA1-like channels enhance glycinergic transmission in medullary dorsal horn neurons.

Journal: Journal of neurochemistry 20120801

Title: Menthol suppresses nicotinic acetylcholine receptor functioning in sensory neurons via allosteric modulation.

Journal: Chemical senses 20120601

Title: Lumbar intervertebral disc degeneration associated with axial and radiating low back pain in ageing SPARC-null mice.

Journal: Pain 20120601

Title: Blockade of TRPM8 activity reduces the invasion potential of oral squamous carcinoma cell lines.

Journal: International journal of oncology 20120501

Title: Modulation of thermoreceptor TRPM8 by cooling compounds.

Journal: ACS chemical neuroscience 20120418

Title: Transient receptor potential vanilloid-1 (TRPV1) is a mediator of lung toxicity for coal fly ash particulate material.

Journal: Molecular pharmacology 20120301

Title: Fused piperidines as a novel class of potent and orally available transient receptor potential melastatin type 8 (TRPM8) antagonists.

Journal: Journal of medicinal chemistry 20120223

Title: Effects of antagonists and heat on TRPM8 channel currents in dorsal root ganglion neuron activated by nociceptive cold stress and menthol.

Journal: Neurochemical research 20120201

Title: Supercooling agent icilin blocks a warmth-sensing ion channel TRPV3.

Journal: TheScientificWorldJournal 20120101

Title: CGRPα-expressing sensory neurons respond to stimuli that evoke sensations of pain and itch.

Journal: PloS one 20120101

Title: The effects of magnetite (Fe₃O₄) nanoparticles on electroporation-induced inward currents in pituitary tumor (GH₃) cells and in RAW 264.7 macrophages.

Journal: International journal of nanomedicine 20120101

Title: The Role of TRP Proteins in Mast Cells.

Journal: Frontiers in immunology 20120101

Title: Expression of transient receptor potential ankyrin 1 (TRPA1) and its role in insulin release from rat pancreatic beta cells.

Journal: PloS one 20120101

Title: Transient receptor potential (TRP) channels as drug targets for diseases of the digestive system.

Journal: Pharmacology & therapeutics 20110701

Title: A novel role for TRPM8 in visceral afferent function.

Journal: Pain 20110701

Title: TRPM8 in mouse sperm detects temperature changes and may influence the acrosome reaction.

Journal: Journal of cellular physiology 20110601

Title: The cannabinoid WIN 55,212-2-mediated protection of dentate gyrus granule cells is driven by CB1 receptors and modulated by TRPA1 and Cav 2.2 channels.

Journal: Hippocampus 20110501

Title: Properties and therapeutic potential of transient receptor potential channels with putative roles in adversity: focus on TRPC5, TRPM2 and TRPA1.

Journal: Current drug targets 20110501

Title: Characterization of TRPM8-like channels activated by the cooling agent icilin in the macrophage cell line RAW 264.7.

Journal: The Journal of membrane biology 20110501

Title: Icilin-evoked behavioral stimulation is attenuated by alpha₂-adrenoceptor activation.

Journal: Brain research 20110412

Title: Icilin induces G1 arrest through activating JNK and p38 kinase in a TRPM8-independent manner.

Journal: Biochemical and biophysical research communications 20110304

Title: Design and optimization of benzimidazole-containing transient receptor potential melastatin 8 (TRPM8) antagonists.

Journal: Journal of medicinal chemistry 20110113

Title: The C-terminal basic residues contribute to the chemical- and voltage-dependent activation of TRPA1.

Journal: The Biochemical journal 20110101

Title: Pharmacological and functional properties of TRPM8 channels in prostate tumor cells.

Journal: Pflugers Archiv : European journal of physiology 20110101

Title: TRPM8 and Nav1.8 sodium channels are required for transthyretin-induced calcium influx in growth cones of small-diameter TrkA-positive sensory neurons.

Journal: Molecular neurodegeneration 20110101

Title: The transient receptor potential family of ion channels.

Journal: Genome biology 20110101

Title: Cooling-sensitive TRPM8 is thermostat of skin temperature against cooling.

Journal: PloS one 20110101

Title: Multimodal assessment of painful peripheral neuropathy induced by chronic oxaliplatin-based chemotherapy in mice.

Journal: Molecular pain 20110101

Title: Update on peripheral mechanisms of pain: beyond prostaglandins and cytokines.

Journal: Arthritis research & therapy 20110101

Title: Sensory properties of menthol and smoking topography.

Journal: Tobacco induced diseases 20110101

Title: TRPM8 biology and medicinal chemistry.

Journal: Current topics in medicinal chemistry 20110101

Title: Activation of TRPA1 by membrane permeable local anesthetics.

Journal: Molecular pain 20110101

Title: Pharmacological blockade of TRPM8 ion channels alters cold and cold pain responses in mice.

Journal: PloS one 20110101

Title: Role of TRPM8 in dorsal root ganglion in nerve injury-induced chronic pain.

Journal: BMC neuroscience 20110101

Title: [Comparative effects of menthol and icilin on the induced contraction of the smooth muscles of the vas deferens of normal and castrated rats].

Journal: Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994) 20110101

Title: Chronic treatment with NGF induces spontaneous fluctuations of intracellular Ca(2+) in icilin-sensitive dorsal root ganglion neurons of the rat.

Journal: The Journal of veterinary medical science 20101201

Title: Expression of transient receptor potential channel vanilloid (TRPV) 1–4, melastin (TRPM) 5 and 8, and ankyrin (TRPA1) in the normal and methimazole-treated mouse olfactory epithelium.

Journal: Acta oto-laryngologica 20101101

Title: Inhibition of the cardiac L-type calcium channel current by the TRPM8 agonist, (-)-menthol.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20101001

Title: Gating of transient receptor potential melastatin 8 (TRPM8) channels activated by cold and chemical agonists in planar lipid bilayers.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100915

Title: Contribution of the S5-pore-S6 domain to the gating characteristics of the cation channels TRPM2 and TRPM8.

Journal: The Journal of biological chemistry 20100827

Title: TRPM8, but not TRPA1, is required for neural and behavioral responses to acute noxious cold temperatures and cold-mimetics in vivo.

Journal: Pain 20100801

Title: Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents.

Journal: Journal of medicinal chemistry 20100722

Title: Intact cutaneous C fibre afferent properties in mechanical and cold neuropathic allodynia.

Journal: European journal of pain (London, England) 20100701

Title: Grueneberg ganglion neurons are finely tuned cold sensors.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100602

Title: (-)-Menthylamine derivatives as potent and selective antagonists of transient receptor potential melastatin type-8 (TRPM8) channels.

Journal: Bioorganic & medicinal chemistry letters 20100501

Title: Modulation of the cold-activated cation channel TRPM8 by surface charge screening.

Journal: The Journal of physiology 20100115

Title: Amiloride-sensitive channels are a major contributor to mechanotransduction in mammalian muscle spindles.

Journal: The Journal of physiology 20100101

Title: The roles of iPLA2, TRPM8 and TRPA1 in chemically induced cold hypersensitivity.

Journal: Molecular pain 20100101

Title: Estrogen regulation of TRPM8 expression in breast cancer cells.

Journal: BMC cancer 20100101

Title: Characterization of selective TRPM8 ligands and their structure activity response (S.A.R) relationship.

Journal: Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques 20100101

Title: Dissociation of μ- and δ-opioid inhibition of glutamatergic synaptic transmission in superficial dorsal horn.

Journal: Molecular pain 20100101

Title: Sensitization of capsaicin and icilin responses in oxaliplatin treated adult rat DRG neurons.

Journal: Molecular pain 20100101

Title: Effects of transient receptor potential (TRP) channel agonists and antagonists on slowly adapting type II mechanoreceptors in the rat sinus hair follicle.

Journal: Journal of the peripheral nervous system : JPNS 20091201

Title: Non-neuronal expression of transient receptor potential type A1 (TRPA1) in human skin.

Journal: The Journal of investigative dermatology 20090901

Title: Letter to the editor: 'Is menthol- or icilin-induced vasodilation mediated by the activation of TRPM8?'.

Journal: American journal of physiology. Heart and circulatory physiology 20090801

Title: Involvement of increased expression of transient receptor potential melastatin 8 in oxaliplatin-induced cold allodynia in mice.

Journal: Neuroscience letters 20090717

Title: Transient receptor potential melastatin 8 channel involvement in the regulation of vascular tone.

Journal: American journal of physiology. Heart and circulatory physiology 20090601

Title: Primary afferents with TRPM8 and TRPA1 profiles target distinct subpopulations of rat superficial dorsal horn neurones.

Journal: British journal of pharmacology 20090601

Title: Dose-dependent effects of icilin on thermal preference in the hindpaw and face of rats.

Journal: The journal of pain : official journal of the American Pain Society 20090601

Title: Comparative modeling of the quaternary structure for the human TRPM8 channel and analysis of its binding features.

Journal: Biochimica et biophysica acta 20090501

Title: Icilin-induced wet-dog shakes in rats are dependent on NMDA receptor activation and nitric oxide production.

Journal: Pharmacology, biochemistry, and behavior 20090501

Title: Lipid raft segregation modulates TRPM8 channel activity.

Journal: The Journal of biological chemistry 20090403

Title: Adult rat odontoblasts lack noxious thermal sensitivity.

Journal: Journal of dental research 20090401

Title: Taste-guided identification of high potency TRPA1 agonists from Perilla frutescens.

Journal: Bioorganic & medicinal chemistry 20090215

Title: Inhibition of TRPM8 by icilin distinct from desensitization induced by menthol and menthol derivatives.

Journal: The Journal of biological chemistry 20090213

Title: Pore dilation occurs in TRPA1 but not in TRPM8 channels.

Journal: Molecular pain 20090101

Title: Inorganic polyphosphate modulates TRPM8 channels.

Journal: PloS one 20090101

Title: Evolution of thermal response properties in a cold-activated TRP channel.

Journal: PloS one 20090101

Title: Tumor necrosis factor-alpha (TNF-alpha) enhances functional thermal and chemical responses of TRP cation channels in human synoviocytes.

Journal: Molecular pain 20090101

Title: Differential role of the menthol-binding residue Y745 in the antagonism of thermally gated TRPM8 channels.

Journal: Molecular pain 20090101

Title: [Modulation of the smooth muscle contractions of the rat vas deferens by TRPM8 channel agonist menthol].

Journal: Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994) 20090101

Title: Impairment by allyl isothiocyanate of gastric epithelial wound repair through inhibition of ion transporters.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20081201

Title: Inhibition by the cold receptor agonists menthol and icilin of airway smooth muscle contraction.

Journal: Pulmonary pharmacology & therapeutics 20081001

Title: Menthol derivative WS-12 selectively activates transient receptor potential melastatin-8 (TRPM8) ion channels.

Journal: Pakistan journal of pharmaceutical sciences 20081001

Title: TRPA1 channels mediate cold temperature sensing in mammalian vagal sensory neurons: pharmacological and genetic evidence.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20080730

Title: Comparison of icilin- and cold-evoked responses of spinal neurones, and their modulation of mechanical activity, in a model of neuropathic pain.

Journal: Brain research 20080618

Title: Plant-derived cannabinoids modulate the activity of transient receptor potential channels of ankyrin type-1 and melastatin type-8.

Journal: The Journal of pharmacology and experimental therapeutics 20080601

Title: ThermoTRP channels in nociceptors: taking a lead from capsaicin receptor TRPV1.

Journal: Current neuropharmacology 20080301

Title: Partial restoration of mutant enzyme homeostasis in three distinct lysosomal storage disease cell lines by altering calcium homeostasis.

Journal: PLoS biology 20080201

Title: Icilin induces a hyperthermia in rats that is dependent on nitric oxide production and NMDA receptor activation.

Journal: European journal of pharmacology 20080114

Title: Molecular and cellular limits to somatosensory specificity.

Journal: Molecular pain 20080101

Title: Citral sensing by Transient [corrected] receptor potential channels in dorsal root ganglion neurons.

Journal: PloS one 20080101

Title: HC-030031, a TRPA1 selective antagonist, attenuates inflammatory- and neuropathy-induced mechanical hypersensitivity.

Journal: Molecular pain 20080101

Title: Contractile effect of TRPA1 receptor agonists in the isolated mouse intestine.

Journal: European journal of pharmacology 20071208

Title: Characterisation of TRPM8 as a pharmacophore receptor.

Journal: Cell calcium 20071201

Title: Differential behavioral effect of the TRPM8/TRPA1 channel agonist icilin (AG-3-5).

Journal: European journal of pharmacology 20071201

Title: Plasticity in intact A delta- and C-fibers contributes to cold hypersensitivity in neuropathic rats.

Journal: Neuroscience 20071130

Title: Impairment by activation of TRPA1 of gastric epithelial restitution in a wound model using RGM1 cell monolayer.

Journal: Inflammopharmacology 20071001

Title: A pharmacological study of slowly adapting mechanoreceptors responsive to cold thermal stimulation.

Journal: Neuroscience 20070824

Title: Regulation of transient receptor potential channels of melastatin type 8 (TRPM8): effect of cAMP, cannabinoid CB(1) receptors and endovanilloids.

Journal: Experimental cell research 20070515

Title: Transient receptor potential channel A1 is directly gated by calcium ions.

Journal: The Journal of biological chemistry 20070504

Title: TRPM8 is required for cold sensation in mice.

Journal: Neuron 20070503

Title: Attenuated cold sensitivity in TRPM8 null mice.

Journal: Neuron 20070503

Title: Modulation of the cold-activated channel TRPM8 by lysophospholipids and polyunsaturated fatty acids.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20070321

Title: Prospects for prostate cancer imaging and therapy using high-affinity TRPM8 activators.

Journal: Cell calcium 20070301

Title: Nalfurafine, the kappa opioid agonist, inhibits icilin-induced wet-dog shakes in rats and antagonizes glutamate release in the dorsal striatum.

Journal: Neuropharmacology 20070301

Title: TRPM8-independent menthol-induced Ca2+ release from endoplasmic reticulum and Golgi.

Journal: The Journal of biological chemistry 20070202

Title: Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines.

Journal: Nature 20070201

Title: Transient receptor potential channel TRPM8 agonists stimulate calcium influx and neurotensin secretion in neuroendocrine tumor cells.

Journal: Neuroendocrinology 20070101

Title: Mice left out in the cold: commentary on the phenotype of TRPM8-nulls.

Journal: Molecular pain 20070101

Title: Species-specific pharmacology of Trichloro(sulfanyl)ethyl benzamides as transient receptor potential ankyrin 1 (TRPA1) antagonists.

Journal: Molecular pain 20070101

Title: The cold and menthol receptor TRPM8 contains a functionally important double cysteine motif.

Journal: The Journal of biological chemistry 20061208

Title: Mu and kappa opioid receptor agonists antagonize icilin-induced wet-dog shaking in rats.

Journal: European journal of pharmacology 20061010

Title: Thermosensitive TRP ion channels mediate cytosolic calcium response in human synoviocytes.

Journal: American journal of physiology. Cell physiology 20060901

Title: Analgesia mediated by the TRPM8 cold receptor in chronic neuropathic pain.

Journal: Current biology : CB 20060822

Title: Functional expression of thermo-transient receptor potential channels in dental primary afferent neurons: implication for tooth pain.

Journal: The Journal of biological chemistry 20060623

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Icilin evokes a dose- and time-dependent increase in glutamate within the dorsal striatum of rats.

Journal: Amino acids 20060501

Title: High-throughput random mutagenesis screen reveals TRPM8 residues specifically required for activation by menthol.

Journal: Nature neuroscience 20060401

Title: Molecular identification and functional characterization of a temperature-sensitive transient receptor potential channel (TRPM8) from canine.

Journal: European journal of pharmacology 20060113

Title: Cool and menthol receptor TRPM8 in human urinary bladder disorders and clinical correlations.

Journal: BMC urology 20060101

Title: Chemosensory properties of murine nasal and cutaneous trigeminal neurons identified by viral tracing.

Journal: BMC neuroscience 20060101

Title: Novel role of cold/menthol-sensitive transient receptor potential melastatine family member 8 (TRPM8) in the activation of store-operated channels in LNCaP human prostate cancer epithelial cells.

Journal: The Journal of biological chemistry 20051125

Title: Icilin activates the delta-subunit of the human epithelial Na+ channel.

Journal: Molecular pharmacology 20051001

Title: Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050420

Title: EGF suppresses hydrogen peroxide induced Ca2+ influx by inhibiting L-type channel activity in cultured human corneal endothelial cells.

Journal: Experimental eye research 20050201

Title: How cold is it? TRPM8 and TRPA1 in the molecular logic of cold sensation.

Journal: Molecular pain 20050101

Title: Two populations of cold-sensitive neurons in rat dorsal root ganglia and their modulation by nerve growth factor.

Journal: The European journal of neuroscience 20041101

Title: The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel.

Journal: Neuron 20040916

Title: TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20040609

Title: Thermosensitive transient receptor potential channels in vagal afferent neurons of the mouse.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20040601

Title: Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.

Journal: British journal of pharmacology 20040201

Title: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures.

Journal: Cell 20030321

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: A TRP channel that senses cold stimuli and menthol.

Journal: Cell 20020308

Title: Identification of a cold receptor reveals a general role for TRP channels in thermosensation.

Journal: Nature 20020307

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